Substituted phenyluracils

ABSTRACT

The invention relates to novel substituted phenyluracils of the general formula (I)in whichR1, R2, R3, R4, R5 and R6 are each as defined in the description,to processes for their preparation, to novel intermediates and to their use as herbicides.

The invention relates to novel substituted phenyluracils, to processesfor their preparation, to novel intermediates and to their use asherbicides.

It is known that certain substituted uracils have herbicidal properties(cf. EP 408382/U.S. Pat. No. 5,084,084/U.S. Pat. No. 5,127,935/U.S. Pat.No. 5,154,755, EP 563384, EP 648749, WO 91/00278, U.S. Pat. No.4,979,982, U.S. Pat. No. 5,169,430, DE 4329537). However, thesecompounds have hitherto not attained any major importance.

This invention, accordingly, provides the novel substitutedphenyluracils of the general formula (I)

in which

R¹ represents hydrogen, halogen or optionally substituted alkyl,

R² represents optionally substituted alkyl,

R³ represents hydrogen, amino or respectively optionally substitutedalkyl, alkenyl or alkinyl,

R⁴ represents hydrogen, cyano or halogen,

R⁵ represents cyano or thiocarbamoyl, and

R⁶ represents one of the groupings below

—C(R⁷,R⁸)—C(R⁷,R⁵)—R⁹ or —C(R⁷)═C(R⁸)—R⁹

in which

R⁷ and R⁸ are identical or different and each represents independentlyof the other hydrogen, hydroxyl, mercapto, halogen or respectivelyoptionally substituted alkyl, alkoxy or alkylthio, and

R⁹ represents cyano, formyl, alkylcarbonyl, the grouping —CO—OR¹⁰ or thegrouping —CO—N(R¹¹,R¹²), where

R¹⁰ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl andheterocyclylalkyl,

R¹¹ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkoxy, alkenyland alkinyl, and

R¹² represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkenyl,alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl andheterocyclylalkyl, or together with R¹¹ represents alkanediyl.

The novel substituted phenyluracils of the general formula (I) areobtained when

(a) aminophenyluracils of the general formula (II)

in which

R¹, R², R³, R⁴ and R⁵ are each as defined above,

or acid adducts of compounds of the formula (II)

are reacted with an alkali metal nitrite or alkyl nitrite and with ahydrogen halide (HX¹) or a metal halide (MX¹), if appropriate in thepresence of a diluent, and the resulting diazonium salts of the generalformula (III)

in which

R¹, R², R³, R⁴ and R⁵ are each as defined above and

X¹ represents halogen,

are reacted with acrylic acid derivatives of the general formula (IV)

C(R⁷,R⁸)═C(R⁷)—R⁹  (IV)

in which

R⁷, R⁸ and R⁹ are each as defined above,

in the presence of hydrogen halides (HX¹), if appropriate in thepresence of catalysts, if appropriate in the presence of water and ifappropriate in the presence of the organic solvent employed initially,

or

(b) substituted phenyluracils of the general formula (Ia)

in which

R¹, R², R³, R⁴, R⁵, R⁷, R⁸ and R⁹ are each as defined above,

but where at least one of the radicals R⁷/R⁸ represents hydrogen and atleast one further radical R⁷/R⁸ in a position vicinal to the firstrepresents halogen

are reacted with an acid acceptor, if appropriate in the presence of adiluent.

It is also possible to convert the compounds of the general formula (I)into other compounds of the general formula (I) according to the abovedefinition using other conventional methods, for example by amination oralkylation (e.g. R³: H→NH₂, H→CH₃), reaction with hydrogen sulphide(e.g. R⁵: CN→CSNH₂), nucleophilic substitution (e.g. R⁸: Cl→SCH₃), ifappropriate addition of hydrogen, halogen or hydrogen halide to a C—Cdouble bond (cf. definition of R⁶), hydrolysis (e.g. R⁹: CN→COOH).

If the compounds of the formula (I) according to the invention containolefinic double bonds (cf. definition of R⁶), the invention relates bothto the individual E and Z or cis and trans isomers separable byconventional methods, and also to any mixtures of these isomers.

The novel substituted phenyluracils of the general formula (I) havestrong herbicidal activity.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkenyl or alkinyl, are in each case straight-chain orbranched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

The invention preferably provides compounds of the formula (I) in which

R¹ represents hydrogen, fluorine, chlorine, bromine or optionallyfluorine- and/or chlorine-substituted C₁-C₄-alkyl,

R² represents optionally fluorine- and/or chlorine-substitutedC₁-C₄-alkyl,

R³ represents hydrogen, amino, represents optionally cyano-, fluorine-,chlorine- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl or representsoptionally fluorine- and/or chlorine-substituted C₂-C₆-alkenyl orC₂-C₆-alkinyl,

R⁴ represents hydrogen, cyano, fluorine or chlorine,

R⁵ represents cyano or thiocarbamoyl, and

R⁶ represents one of the groupings below

—C(R⁷,R⁸)—C(R⁷,R⁸)—R⁹ or —C(R⁷)═C(R⁸)—R⁹

in which

R⁷ and R⁸ are identical or different and each represents independentlyof the other hydrogen, hydroxyl, mercapto, fluorine, chlorine, bromineor respectively optionally cyano-, fluorine-, chlorine- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio,and

R⁹ represents cyano, formyl, C₁-C₄-alkyl-carbonyl, the grouping —CO—OR¹⁰or the grouping —CO—N(R¹¹,R¹²), where

R¹⁰ represents hydrogen or represents optionally cyano-, fluorine-,chlorine- or C₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl,

R¹⁰ furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted C₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl,

R¹⁰ furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substitutedC₃-C₆-cycloalklyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

R¹⁰ furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxaazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl,

R¹¹ represents hydrogen or represents respectively optionally cyano-,fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl orC₁-C₆-alkoxy,

R¹¹ furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted C₃-C₆-alkenyl or C₃-C₆-alkinyl, and

R¹² represents hydrogen or represents optionally cyano-, fluorine-,chlorine- or C₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl,

R¹² furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted C₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl,

R¹² furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substitutedC₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl,

R¹² furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C_(l)-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio,C₁-C₄-halogenoalkylthio- or C₁-C₄-alkoxy-carbonyl-substituted phenyl,phenyl-C₁-C₄-alkyl, furyl, furylmethyl, tetrahydrofuryl,tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl,tetrahydrothienylmethyl, perhydropyranyl, perhydropyranylmethyl,oxazolyl, oxadiazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl,oxadiazolylmethyl, thiadiazolyl, thiadiazolylmethyl, dioxolanyl,dioxolanylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl orpyrimidinylmethyl or together with R¹¹ represents C₂-C₆-alkanediyl.

The invention in particular provides compounds of the formula (I) inwhich

R¹ represents hydrogen, fluorine, chlorine, bromine or optionallyfluorine- and/or chlorine-substituted methyl or ethyl,

R² represents optionally fluorine- and/or chlorine-substituted methyl orethyl,

R³ represents hydrogen, amino, represents optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, or represents optionally fluorine- and/orchlorine-substituted propenyl, butenyl, propinyl or butinyl,

R⁴ represents hydrogen, fluorine or chlorine,

R⁵ represents cyano or thiocarbamoyl, and

R⁶ represents one of the groupings below

—C(R⁷,R⁸)—C(R⁷,R⁸)—R⁹ or —C(R⁷)═C(R⁸)—R⁹

in which

R⁷ and R⁸ are identical or different and each represents independentlyof the other hydrogen, fluorine, chlorine, bromine or respectivelyoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, methoxy, ethoxy, methylthio or ethylthio, and

R⁹ represents cyano, the grouping —CO—OR¹⁰ or the grouping—CO—N(R¹¹,R¹²), where

R¹⁰ represents hydrogen or represents respectively optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl,

R¹⁰ furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted propenyl, butenyl, pentenyl, propinyl, butinyl orpentinyl,

R¹⁰ furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, methoxycarbonyl- orethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl,

R¹⁰ furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-,ethoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-,difluoromethylthio-, trifluoromethyl-, methoxycarbonyl- orethoxycarbonyl-substituted phenyl, phenylmethyl, phenylethyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl,

R¹¹ represents hydrogen or represents respectively optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,methoxy or ethoxy,

R¹¹ furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted propenyl or propinyl, and

R¹² represents hydrogen or represents optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl,

R¹² furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted propenyl, butenyl, pentenyl, propinyl, butinyl orpentinyl, represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, methoxycarbonyl- orethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclo-butylmethyl, cyclopentylmethyl orcyclohexylmethyl,

R¹² furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, trifluoromethyl-, methoxy-,ethoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-,difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl- orethoxycarbonyl-substituted phenyl, phenylmethyl, phenylethyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl.

The general or preferred radical definitions listed above are valid bothfor the end products of the formula (I) and, in a corresponding manner,also for the starting materials or intermediates which are required ineach case for the preparation. These radical definitions can be combinedwith each other at will, i.e. combinations between the given preferredranges are also possible.

Examples of the compounds of the formula (I) according to the inventionare listed in the groups below.

Group 1

R⁶ has in this case for example the meanings given in the list below:

2-cyano-ethenyl, 2-cyano-1-methyl-ethenyl, 2-cyano-1-chloro-ethenyl,2-cyano-2-chloro-ethenyl, 2-cyano-1-bromo-ethenyl,2-cyano-2-bromo-ethenyl, 2-cyano-propenyl, 2-cyano-ethyl,2-cyano-2-fluoro-ethyl, 2-cyano-2-chloro-ethyl, 2-cyano-2-bromo-ethyl,2-cyano-1,2-dichloro-ethyl, 2-cyano-1,2-dibromo-ethyl,2-cyano-2,2-dichloro-ethyl, 2-cyano-2-chloro-1-methyl-ethyl,2-cyano-2-chloro-1,2-dimethyl-ethyl, 2-cyano-2-chloro-propyl,2-carboxy-ethenyl, 2-carboxy-l-methyl-ethenyl,2-carboxy-1-chloro-ethenyl, 2-carboxy-2-chloro-ethenyl,2-carboxy-1-bromo-ethenyl, 2-carboxy-2-bromo-ethenyl,2-carboxy-propenyl, 2-carboxy-ethyl, 2-carboxy-2-fluoro-ethyl,2-carboxy-2-chloro-ethyl, 2-carboxy-2-bromo-ethyl,2-carboxy-1,2-dichloro-ethyl, 2-carboxy-1,2-dibromo-ethyl,2-carboxy-2,2-dichloro-ethyl, 2-carboxy-2-chloro-1-methyl-ethyl,2-carboxy-2-chloro-1,2-dimethyl-ethyl, 2-carboxy-2-chloro-propyl,2-methoxycarbonyl-ethenyl, 2-methoxycarbonyl-1-methyl-ethenyl,2-methoxycarbonyl-1-chloro-ethenyl, 2-methoxycarbonyl-2-chloro-ethenyl,2-methoxycarbonyl-1-bromo-ethenyl, 2-methoxycarbonyl-2-bromo-ethenyl,2-methoxycarbonyl-propenyl, 2-methoxycarbonyl-ethyl,2-methoxycarbonyl-2-fluoro-ethyl, 2-methoxycarbonyl-2-chloro-ethyl,2-methoxycarbonyl-2-bromo-ethyl, 2-methoxycarbonyl-1,2-dichloro-ethyl,2-methoxycarbonyl-1,2-dibromo-ethyl,2-methoxycarbonyl-2,2-dichloro-ethyl,2-methoxycarbonyl-2-chloro-1-methyl-ethyl,2-methoxycarbonyl-2-chloro-1,2-dimethyl-ethyl,2-methoxycarbonyl-2-chloro-propyl, 2-ethoxycarbonyl-ethenyl,2-ethoxycarbonyl-1-methyl-ethenyl, 2-ethoxycarbonyl-1-chloro-ethenyl,2-ethoxycarbonyl-2-chloro-ethenyl, 2-ethoxycarbonyl-1-bromo-ethenyl,2-ethoxycarbonyl-2-bromo-ethenyl, 2-ethoxycarbonyl-propenyl,2-ethoxycarbonyl-ethyl, 2-ethoxycarbonyl-2-fluoro-ethyl,2-ethoxycarbonyl-2-chloro-ethyl, 2-ethoxycarbonyl-2-bromo-ethyl,2-ethoxycarbonyl-1,2-dichloro-ethyl, 2-ethoxycarbonyl-1,2-dibromo-ethyl,2-ethoxycarbonyl-2,2-dichloro-ethyl,2-ethoxycarbonyl-2chloro-1-methyl-ethyl,2-ethoxycarbonyl-2-chloro-1,2-dimethyl-ethyl,2-ethoxycarbonyl-2-chloro-propyl.

Group 2

R⁶ has in this case for example the meanings listed above in Group 1.

Group 3

R⁶ has in this case for example the meanings listed above in Group 1.

Group 4

R⁶ has in this case for example the meanings listed above in Group 1.

Group 5

R⁶ has in this case for example the meanings listed above in Group 1.

Group 6

R⁶ has in this case for example the meanings listed above in Group 1.

Group 7

R⁶ has in this case for example the meanings listed above in Group 1.

Group 8

R⁶ has in this case for example the meanings listed above in Group 1.

Group 9

R⁶ has in this case for example the meanings listed above in Group 1.

Group 10

R⁶ has in this case for example the meanings listed above in Group 1.

Group 11

R⁶ has in this case for example the meanings listed above in Group 1.

Group 12

R⁶ has in this case for example the meanings listed above in Group 1.

Group 13

R⁶ has in this case for example the meanings listed above in Group 1.

Group 14

R⁶ has in this case for example the meanings listed above in Group 1.

Group 15

R⁶ has in this case for example the meanings listed above in Group 1.

Group 16

R⁶ has in this case for example the meanings listed above in Group 1.

Group 17

R⁶ has in this case for example the meanings listed above in Group 1.

Group 18

R⁶ has in this case for example the meanings listed above in Group 1.

Group 19

R⁶ has in this case for example the meanings listed above in Group 1.

Group 20

R⁶ has in this case for example the meanings listed above in Group 1.

Group 21

R⁶ has in this case for example the meanings listed above in Group 1.

Group 22

R⁶ has in this case for example the meanings listed above in Group 1.

Using, for example,1-(5-amino-4-cyano-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine,sodium nitrite and hydrochloric acid and then methyl acrylate asstarting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following scheme:

Using, for example,1-[4-cyano-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2,6-dioxo-3,5-dimethyl-4-trifluoromethyl-1(2H)-pyrimidineas starting material and triethylamine as acid acceptor, the course ofthe reaction in the process (b) according to the invention can beillustrated by the following scheme:

The formula (II) provides a general definition of the aminophenyluracilsto be used as starting materials in the process (a) according to theinvention for preparing the compounds of the formula (I). In the formula(II), R¹, R², R³, R⁴ and R⁵ each preferably or in particular have thosemeanings which have already been indicated above, in connection with thedescription of the compounds of the formula (I) to be prepared accordingto the invention, as being preferred or particularly preferred for R¹,R², R³, R⁴ and R⁵.

The starting materials of the formula (II) are known and/or can beprepared by processes known per se (cf. EP 648749, PreparationExamples).

The formula (IV) provides a general definition of the acrylic acidderivatives further to be used as starting materials in the process (a)according to the invention for preparing compounds of the formula (I) Inthe formula (IV), R⁷, R⁸ and R⁹ each preferably or in particular havethose meanings which have already been indicated above, in connectionwith the description of the compounds of the formula (I) to be preparedaccording to the invention, as being preferred or particularly preferredfor R⁷, R⁸, and R⁹.

The starting materials of the formula (IV) are known organic chemicalsfor synthesis.

The formula (III) provides a general definition of the diazonium saltsformed as intermediates in the process (a) according to the inventionfor preparing the compounds of the formula (I). In the formula (III),R¹, R², R³, R⁴ and R⁵ each preferably or in particular have thosemeanings which have already been indicated above, in connection with thedescription of the compounds of the formula (I) to be prepared accordingto the invention, as being preferred or particularly preferred for R¹,R², R³, R⁴ and R⁵; X¹ preferably represents fluorine, chlorine, bromineor iodine, in particular chlorine or bromine.

The compounds of the formula (III) have not yet been disclosed in theliterature; as novel substances, they form part of the subject-matter ofthe present application.

The formula (Ia) provides a general definition of the substitutedphenyluracils to be used as starting materials in the process (b)according to the invention for preparing the compounds of the formula(I). In the formula (Ia), R¹, R², R³, R⁴, R⁵, R⁷, R⁸ and R⁹ eachpreferably or in particular have those meanings which have already beenindicated above, in connection with the description of the compounds ofthe formula (I) to be prepared according to the invention, as beingpreferred or particularly preferred for R¹, R², R³, R⁴, R⁵, R⁷, R⁸ andR⁹.

The starting materials of the formula (Ia) are novel compounds accordingto the invention; they can be prepared by the process (a) according tothe invention.

The process (a) according to the invention is carried out using analkali metal nitrite or alkyl nitrite. These are preferably lithiumnitrite, sodium nitrite, potassium nitrite, rubidium nitrite and caesiumnitrite, methyl nitrite, ethyl nitrite, n- or i-propyl nitrite, n-, i-,s- or t-butyl nitrite, n-, i-, s- or t-pentyl nitrite, in particularsodium nitrite, potassium nitrite, methyl nitrite, n-, i-, s- or t-butylnitrite, n-, i-, s- or t-pentyl nitrite.

The process according to the invention is carried out using a hydrogenhalide (HX¹) or a metal halide (MX¹). These are preferably hydrogenfluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide,copper(I) chloride, copper(II) chloride and copper(I) bromide, inparticular hydrogen chloride and hydrogen bromide, copper(I) chloride,copper(II) chloride and copper(I) bromide.

The process (a) according to the invention for preparing compounds ofthe formula (I) is preferably carried out in the presence of a diluent.Suitable diluents are generally the customary organic solvents. Theseinclude preferably aliphatic, alicyclic and aromatic, optionallyhalogenated hydrocarbons such as, for example, pentane, hexane, heptane,petroleum ether, ligroin, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane,dichloromethane (methylene chloride), trichloromethane (chloroform) orcarbon tetrachloride, dialkyl ethers such as, for example, diethylether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butylether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether,tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether orethylene glycol diethyl ether, diethylene glycol dimethyl ether ordiethylene glycol diethyl ether; dialkyl ketones such as, for example,acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone ormethyl i-butyl ketone, nitriles such as, for example, acetonitrile,propionitrile, butyronitrile or benzonitrile; amides such as, forexample, N,N-dimethyl-formamide (DM), N,N-dimethyl-acetamide,N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorictriamide; esters such as, for example, methyl acetate, ethyl acetate, n-or i-propyl acetate, n-, i- or s-butyl acetate; sulphoxides such as, forexample, dimethyl sulphoxide; alkanols such as, for example, methanol,ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycolmonomethyl ether or ethylene glycol monoethyl ether, diethylene glycolmonomethyl ether or diethylene glycol monoethyl ether; (monophasic ormultiphasic) mixtures thereof with water or pure water.

When carrying out the process (a) according to the invention, thereaction temperatures can be varied over a relatively wide range. Ingeneral, temperatures between −20° C. and +100° C., preferably between−10° C. and +80° C., in particular between 0° C. and 60° C., areemployed.

The process (a) according to the invention is generally carried outunder atmospheric pressure. However, it is also possible to carry outthe process according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

In the practice of the process (a) according to the invention, thestarting materials are generally employed in approximately equimolaramounts. However, it is also possible to use one of the components in arelatively large excess. The reaction is generally carried out in asuitable diluent and the reaction mixture is generally stirred forseveral hours at the temperature required. Work-up is carried outaccording to customary methods (cf. the Preparation Examples).

The process (b) according to the invention for preparing compounds ofthe formula (I) is preferably carried out in the presence of a suitableacid acceptor. Suitable acid acceptors are generally the customaryinorganic or organic bases. These include preferably alkali metal oralkaline earth metal acetates, amides, carbonates, bicarbonates,hydrides, hydroxides or alkoxides such as, for example, sodium acetate,potassium acetate or calcium acetate, lithium amide, sodium amide,potassium amide or calcium amide, sodium carbonate, potassium carbonateor calcium carbonate, sodium bicarbonate, potassium bicarbonate orcalcium bicarbonate, lithium hydride, sodium hydride, potassium hydrideor calcium hydride, lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, sodium methoxide or potassium methoxide,sodium ethoxide or potassium ethoxide, sodium n- or i-propoxide orpotassium n- or i-propoxide, sodium n-, i-, s- or t-butoxide orpotassium n-, i-, s- or t-butoxide; furthermore also basic organicnitrogen compounds such as, for example, trimethylamine, triethylamine,tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine,1,4-diazabicyclo[2,2,2]-octane (DABCO),1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), and 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU).

The process (b) according to the invention for preparing compounds ofthe formula (I) is preferably carried out in the presence of a diluent.Suitable diluents are generally the customary organic solvents. Theseinclude preferably aliphatic, alicyclic and aromatic, optionallyhalogenated hydrocarbons such as, for example, pentane, hexane, heptane,petroleum ether, ligroin, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane,dichloromethane (methylene chloride), trichloromethane (chloroform) orcarbon tetrachloride, dialkyl ethers such as, for example, diethylether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butylether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether,tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether orethylene glycol diethyl ether, diethylene glycol dimethyl ether ordiethylene glycol diethyl ether; dialkyl ketones such as, for example,acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone ormethyl i-butyl ketone, nitrites such as, for example, acetonitrile,propionitrile, butyronitrile or benzonitrile; amides such as, forexample, N,N-dimethyl-formamide (DMF), N,N-dimethyl-acetamide,N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphorictriamide; esters such as, for example, methyl acetate, ethyl acetate, n-or i-propyl acetate, n-, i- or s-butyl acetate; sulphoxides such as, forexample, dimethyl sulphoxide; alkanols such as, for example, methanol,ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycolmonomethyl ether or ethylene glycol monoethyl ether, diethylene glycolmonomethyl ether or diethylene glycol monoethyl ether; mixtures thereofwith water or pure water.

When carrying out the process (1) according to the invention, thereaction temperatures can be varied over a relatively wide range. Ingeneral, temperatures of between −10° C. and 120° C., preferably between0° C. and 90° C., in particular between 10° C. and 60° C., are employed.

The process (b) according to the invention is generally carried outunder atmospheric pressure. However, it is also possible to carry outthe process according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

In the practice of the process (b) according to the invention, thestarting materials are generally employed in approximately equimolaramounts. However, it is also possible to use one of the components in arelatively large excess. The reaction is generally carried out in asuitable diluent in the presence of a reaction auxiliary, and thereaction mixture is generally stirred for several hours at thetemperature required. Work-up is carried out according to customarymethods (cf. the Preparation Examples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm-killers and, especially, as weed-killers.Weeds, in the broadest sense, are all plants which grow in locationswhere they are undesired. Whether the compounds according to theinvention act as total or selective herbicides depends essentially onthe amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium. However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

The compounds of the formula (I) according to the invention areparticularly suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops bothby the pre- and the post-emergence method.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine encapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If water is used as extender, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents include: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates,suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, and synthetic granules of inorganic and organic meals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifiers and/or foam-formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or,in their formulations, also as a mixture with known herbicides for thecontrol of weeds, in which case ready-to-use formulations or tank mixesare possible.

Suitable co-components for the mixtures are known herbicides, forexample anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4 D,2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylaminessuch as, for example, alloxydim, clethodim, cycloxydim, sethoxydim andtralkoxydim; imidazolinones such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example,mefenacet, sulphonylureas such as, for example, amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates such as, for example, butylate, cycloate, di-allate,EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate;triazines such as, for example, atrazine, cyanazine, simazine,simetryne, terbutryne and terbutylazine; triazinones such as, forexample, hexazinone, metamitron and metribuzin; others such as, forexample, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

Process (a)

A mixture of 1.8 g (21 mmol) of methyl acrylate, 1.6 g (15.5 mmol) oft-butyl nitrite, 1.6 g (12 mmol) of copper(II) chloride and 50 ml ofacetonitrile is cooled to about 0° C., and a solution of 3.3 g (10 mmol)of1-(5-amino-4-cyano-2-fluorophenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine in 20 ml of acetonitrile is added dropwise at thistemperature. The reaction mixture is then allowed to warm to roomtemperature and stirred at this temperature for 18 hours. After theaddition of 20 ml of 1N hydrochloric acid, the mixture is then extractedwith ethyl acetate and the organic phase is dried with sodium sulphateand filtered. The filtrate is concentrated and the residue is worked-upby column chromatography.

2.8 g (65% of theory) of1-[4-cyano-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidineof melting point 46° C. are obtained.

Example 2

Process (b)

0.22 g of sodium hydride (60%) are added with stirring to a mixture of2.0 g (4.6 mmol) of1-[4-cyano-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyltrifluoromethyl-1(2H)-pyrimidineand 30 ml of N,N-dimethyl-formamide which had been cooled to 0° C., andthe reaction mixture is initially stirred for 15 minutes at 0° C., thenfor about 60 minutes at 20° C. and finally for 6 hours at 60° C. Themixture is then concentrated using waterpump vacuum, the residue isstirred with diisopropyl ether and the crystalline product is isolatedby filtration with suction.

1.1 g (60% of theory) of1-[4-cyano-2-fluoro-5-(2-methoxycarbonyl-ethenyl)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidineof melting point 154° C. are obtained.

By the methods of Examples 1 and 2 and according to the generaldescription of the preparation processes according to the invention, itis also possible to prepare, for example, the compounds of the formula(I) listed in Table 1 below.

TABLE 1 Examples of compounds of the formula (I) (I)

Ex. Melting No. R¹ R² R³ R⁴ R⁵ R⁶ point (° C.) 3 H CF₃ CH₃ H CN

4 H CF₃ CH₃ F CSNH₂

5 H CF₃ CH₃ F CN

6 H CF₃ CH₃ F CN

7 H CF₃ CH₃ F CN

8 H CF₃ CH₃ F CN

9 H CF₃ CH₃ F CN

10 H CF₃ CH₃ F CN

11 H CF₃ CH₃ F CN

12 H CF₃ CH₃ F CN

13 H CF₃ CH₃ F CN

186 14 H CF₃ CH₃ F CN

175 15 H CF₃ CH₃ F CN

85 16 H CF₃ CH₃ F CN

17 H CF₃ CH₃ F CN

18 H CF₃ CH₃ F CSNH₂

19 H CF₃ CH₃ F CSNH₂

20 CH₃ CF₃ CH₃ F CN

21 H CF₃ CH₃ F CN

22 H CF₃ CH₃ F CN

23 H CF₃ CH₃ F CN

173 24 H CF₃ CH₃ F CN

159 25 H CF₃ CH₃ F CN

186 26 H CF₃ CH₃ F CN

27 H CF₃ CH₃ F CN

197

STARTING MATERIALS OF THE FORMULA (II) Example (II-1)

0.17 g (1.2 mmol) of pivaloyl chloride is added with stirring to amixture of 0.50 g (1.2 mmol) of1-(4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine,1 ml of triethylamine and 50 ml of acetonitrile, and the reactionmixture is stirred for 18 hours at 20° C. and for a further 15 hours at60° C. The mixture is then concentrated using waterpump vacuum, theresidue is shaken with 1N hydrochloric acid/ethyl acetate and theorganic phase is separated off, dried with sodium sulphate and filtered.The filtrate is concentrated using waterpump vacuum and the residue isworked-up by column chromatography (silica gel, chloroform/ethylacetate, 1:1 (v:v)).

In addition to unreacted1-(4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine(first fraction: 0.30 g), 0.2 g (50% of theory) of1-(4-cyano-2-fluoro-5-amino-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidineis obtained as second fraction. Melting point: 195° C.

USE EXAMPLES Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, thesoil is watered with the preparation of the active compound. It isadvantageous to keep the amount of water per unit area constant. Theconcentration of the active compound in the preparation is immaterial,only the amount of active compound applied per unit area matters.

After three weeks, the degree of damage to the plants is rated in %damage by comparison with the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%/=total destruction

In this test, strong activity against weeds was shown by the compoundsof the formula (I).

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the particulardesired amounts of active compound are applied in about 1000 l/ha.

After three weeks, the degree of damage to the plants is rated in %damage by comparison with the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, strong activity against weeds such as Abutilon (100%),Amaranthus (100%), Galium (100%), Xanthium (100%), Setaria (100%) andAvena fatua (95%) is shown by the compounds of Preparation Examples 1and 2 at application rates of 125 g/ha.

What is claimed is:
 1. A compound of formula (I)

wherein R¹ represents hydrogen, fluorine, chlorine, bromine oroptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl, R²represents optionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl,R³ represents hydrogen, amino, optionally cyano-, chlorine- orC₁-C₄-alkoxy-substituted C₁-C₆-alkyl or optionally fluorine- and/orchlorine-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, R⁴ representshydrogen, cyano, fluorine or chlorine, R⁵ represents cyano orthiocarbamoyl, and R⁶ represents one of the groupings belowC(R⁷,R⁸)—C(R⁷,R⁸)—R⁹ or —C(R⁷)═C(R⁸)—R⁹ in which R⁷ and R⁸ are identicalor different and each represents independently of the other hydrogen,hydroxyl, mercapto, fluorine, chlorine, bromine or respectivelyoptionally cyano-, fluorine-, chlorine- or C₁-C₄-alkoxy-substitutedC₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄- alkylthio, and R⁹ represents cyano,formyl, C₁-C₄-alkylcarbonyl, the grouping —CO—OR¹⁰ or the grouping—CO—N(R¹¹,R¹²), where R¹⁰ represents hydrogen or represents optionallycyano-, fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl,R¹⁰ furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted C₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl, R¹⁰ furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substitutedC₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, R¹⁰ furthermorerepresents respectively optionally cyano-, fluorine, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanyl methyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl, R¹¹represents hydrogen or represents respectively optionally cyano-,fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl orC₁-C₆-alkoxy, R¹¹ furthermore represents respectively optionallyfluorine-, chlorine- or bromine-substituted C₃-C₆-alkenyl orC₃-C₆-alkinyl, and R¹² represents hydrogen or represents optionallycyano-, fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl,R¹² furthermore represents respectively optionally fluorine-, chlorine-or bromide-substituted C₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl, R¹² furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substitutedC₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, R¹² furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl or togetherwith R¹¹ represents C₂-C₆-alkanediyl.
 2. The compound according to claim1 wherein R¹ represents hydrogen, fluorine, chlorine, bromine oroptionally fluorine and/or chlorine-substituted methyl or ethyl, R²represents optionally fluorine- and/or chlorine-substituted methyl orethyl, R³ represents hydrogen, amino, represents optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, - or t-butyl, or represents optionally fluorine-and/or chlorine-substituted propenyl, butenyl, propinyl or butinyl, R⁴represents hydrogen, fluorine or chlorine, R⁵ represents cyano orthiocarbamoyl, and R⁶ represents one of the groupings below—C(R⁷,R⁸)—C(R⁷,R⁸)—R⁹ or —C(R⁷)═C(R⁸)—R⁹ in which R⁷ and R⁸ areidentical or different and each represents independently of the otherhydrogen, fluorine, chlorine, bromine or respectively optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,methoxy, ethoxy, methylthio or ethylthio, and R⁹ represents cyano, thegrouping —CO—OR¹⁰ or the grouping —CO—N(R¹¹,R¹²), where R¹⁰ representshydrogen or represents optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, n-, i-, s- or t-pentyl, R¹⁰ furthermore represents respectivelyoptionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, pentenyl, propinyl, butinyl or pentinyl, R¹⁰ furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, methoxycarbonyl- orethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, R¹⁰ furthermore represents respectively optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, difluoromethylthio-,trifluoromethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted phenyl,phenylmethyl, phenylethyl, furyl, furylmethyl, tetrahydrofuryl,tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl,tetrahydrothienylmethyl, perhydropyranyl, perhydropyranylmethyl,oxazolyl, oxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl,oxadiazolylmethyl, thiadiazolyl, thiadiazolylmethyl, dioxolanyl,dioxolanylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl orpyrimidinylmethyl, R¹¹ represents hydrogen or represents respectivelyoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, methoxy or ethoxy, R¹¹ furthermore representsrespectively optionally fluorine-, chlorine- or bromine-substitutedpropenyl or propinyl, and R¹² represents hydrogen or representsoptionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- ort-pentyl, R¹² furthermore represents respectively optionally fluorine-,chlorine- or bromine-substituted propenyl butenyl, pentenyl, propinyl,butinyl or pentinyl, respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, methoxycarbonyl- orethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclo-butylmethyl, cyclopentylmethyl orcyclohexylmethyl, R¹² furthermore represents respectively optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, difluoromethylthio-,trifluoromethylthio-, methoxycarbonyl- or ethoxycarbonyl-substitutedphenyl, phenylmethyl, phenylethyl, furyl, furylmethyl, tetrahydrofuryl,tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl,tetrahydrothienylmethyl, perhydropyranyl, perhydropyranylmethyl,oxazolyl, oxazolylmethyl thiazolyl, thiazolylmethyl, oxadiazolyl,oxadiazolylmethyl, thiadiazolyl, thiadiazolylmethyl, dioxolanyl,dioxolanylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl orpyrimidinylmethyl.
 3. An herbicidal composition comprising anherbicidally effective amount of a compound according to claim 1 and anextender or surfactant.
 4. A method of controlling unwanted vegetationwhich comprises applying to such vegetation or to a locus from which itis desired to exclude such vegetation an herbicidally effective amountof a compound according to claim
 1. 5. A compound of the formula (III):

wherein R¹ represents hydrogen, fluorine, chlorine, bromine oroptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl, R²represents optionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl,R³ represents hydrogen, amino, optionally cyano-, fluorine-, chlorine-or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl or optionally fluorine- and/orchlorine-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, R⁴ representshydrogen cyano, fluorine or chlorine, R⁵ represents cyano orthiocarbamoyl, and X¹ represents halogen.
 6. A compound of the formula(Ia):

wherein R¹ represents hydrogen, fluorine, chlorine, bromine oroptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl, R²represents optionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl,R³ represents hydrogen, amino, optionally cyano-, fluorine-, chlorine-or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl or optionally fluorine- and/orchlorine-substituted C₂-C₆-alkenyl or C₁-C₆-alkinyl, R⁴ representshydrogen, cyano, fluorine or chlorine, R⁵ represents cyano orthiocarbamoyl, and R⁶ represents one of the groupings below—C(R⁷,R⁸)—C(R⁷,R⁸)—R⁹ or —C(R⁷)═C(R⁸)—R⁹ in which R⁷ and R⁸ areidentical or different and each represents independently of the otherhydrogen, hydroxyl, mercapto, fluorine, chlorine, bromine orrespectively optionally cyano-, fluorine-, chlorine- orC₁-C₄-alkoxy-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio,and R⁹ represents cyano, formyl, C₁-C₄-alkyl-carbonyl, the grouping—CO—OR¹⁰ or the grouping —CO—N(R¹¹,R¹²), where R¹⁰ represents hydrogenor represents optionally cyano-, fluorine-, chlorine- orC₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl, R¹⁰ furthermore representsrespectively optionally fluorine-, chlorine- or bromine-substitutedC₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl, R¹⁰ furthermore representsrespectively optionally cyano-, fluorine-, chlorine-, bromine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substituted C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₄-alkyl, R¹⁰ furthermore represents respectivelyoptionally cyano-, fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-,C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxadiazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl, R¹¹represents hydrogen or represents respectively optionally cyano-,fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl orC₁-C₆-alkoxy, R¹¹ furthermore represents respectively optionallyfluorine-, chlorine- or bromine-substituted C₃-C₆-alkenyl orC₃-C₆-alkinyl, and R¹² represents hydrogen or represents optionallycyano-, fluorine-, chlorine- or C₁-C₄-alkoxy-substituted C₁-C₁₀-alkyl,R¹² furthermore represents respectively optionally fluorine-, chlorine-or bromine-substituted C₃-C₁₀-alkenyl or C₃-C₁₀-alkinyl, R¹² furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-carbonyl-substitutedC₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, R¹² furthermorerepresents respectively optionally cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyl-C₁-C₄-alkyl, furyl,furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl,thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl,perhydropyranyl, perhydropyranylmethyl, oxazolyl, oxadiazolylmethyl,thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazolylmethyl,thiadiazolyl, thiadiazolylmethyl, dioxolanyl, dioxolanylmethyl,pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl or togetherwith R¹¹ represents C₂-C₆-alkanediyl.